Methanol → N,N'-bis-[2,3-dihydroxypropyl]-5-[3-hydroxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

HRID 233065Notes

Reaction equation

HRID 233065 reaction equation
C([O:4][CH:5]([CH2:43][O:44]C(=O)C)[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[CH2:21][CH2:20][CH:19]([O:22]C(=O)C)[C:18]2=[O:26])[C:13]([I:27])=[C:12]([C:28]([NH:30][CH2:31][CH:32]([O:38]C(=O)C)[CH2:33][O:34]C(=O)C)=[O:29])[C:11]=1[I:42])=[O:9])(=O)C.C[O-].[Na+].CO.CCC1(C2C=CC(N)=CC=2)C(=O)NC(=O)CC1>O>[OH:4][CH:5]([CH2:43][OH:44])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[CH2:21][CH2:20][CH:19]([OH:22])[C:18]2=[O:26])[C:13]([I:27])=[C:12]([C:28]([NH:30][CH2:31][CH:32]([OH:38])[CH2:33][OH:34])=[O:29])[C:11]=1[I:42])=[O:9]

Participants

6

Reactant 4

HCID 887MethanolHCID 2145Aminoglutethimide2×HCID 10942334Sodium MethoxideHCID 19048410N,N'-bis-[2,3-diacetyloxypropyl]-5-[3-acetyloxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide

Product 1

HCID 11803402N,N'-bis-[2,3-dihydroxypropyl]-5-[3-hydroxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamideYield 71.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N,N'-Bis-[2,3-diacetyloxypropyl]-5-[3-acetyloxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide of example 5b (4.20 g, 4.20 mmol) was treated with a 0.105M solution of methanolic sodium methoxide [prepared by the addition of Na metal (48 mg, 2.10 mmol) to dry methanol (20 ml)] under a nitrogen atmosphere for 2.5 hours. The pH was then adjusted to 6.70 using Dowex-50 resin (H+ form) and AG-1 (OH- form) as necessary. The resin was removed and the solvents evaporated to give a yellow oil. This product was dissolved in 20 ml of deionized water and the pH adjusted to 6.98 by the addition of AG-1 (OH- 1 form) resin. The resin was filtered off and the filtrate containing the crude product was purified by low pressure reverse phase column chromatography using a CHP-20 resin to obtain N,N'-bis-[2,3-dihydroxypropyl]-5-[3-hydroxy-2-oxo-1-pyrrolidinyl]-2,4,6-triiodo-1,3-benzenedicarboxamide as a white foam (2.36 g, 71% yield).

Workup

  1. customThe resin was removed
  2. customthe solvents evaporated
  3. customto give a yellow oil
  4. filtrationThe resin was filtered off
  5. additionthe filtrate containing the crude product
  6. customwas purified by low pressure reverse phase column chromatography

Sources & evidence

ORD record
ord-29f3d9515d0a43e08229124bda5d04a2
Source dataset
uspto-grants-1997_01
Patent number
US05591846

Reaction notes

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